Hydrochloric Acid → Benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylate

HRID 569404Notes

Reaction equation

HRID 569404 reaction equation
[I-].[CH:2]([O:15][C:16]([C:18]1[N:23]2[C:24](=[O:48])[CH:25]([NH:26][C:27](=[O:47])[C:28](=[N:37][O:38][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:29]3[N:30]=[C:31]([NH:34][CH:35]=[O:36])[S:32][CH:33]=3)[C@H:22]2[S:21][CH2:20][C:19]=1[CH2:49][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:69](=O)([O-])[O-].[Na+].[Na+].Cl>C(Cl)Cl.O.C=O>[C:43]([O:42][C:40]([CH2:39][O:38][N:37]=[C:28]([C:29]1[N:30]=[C:31]([NH:34][CH:35]=[O:36])[S:32][CH:33]=1)[C:27]([NH:26][CH:25]1[C:24](=[O:48])[N:23]2[C:18]([C:16]([O:15][CH:2]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[O:17])=[C:19]([CH:49]=[CH2:69])[CH2:20][S:21][C@H:22]12)=[O:47])=[O:41])([CH3:45])([CH3:44])[CH3:46]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 131713183[4-Benzhydryloxycarbonyl-7-{2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido}-3-cephem-3-yl]methyl triphenyl-phosphonium iodide

Product 1

HCID 131713176Benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylate

Reagents, catalysts & solvents 3

HCID 712FormaldehydeSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

[4-Benzhydryloxycarbonyl-7-{2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido}-3-cephem-3-yl]methyltriphenyl-phosphonium iodide (syn isomer)(0.59 g) was dissolved in a mixture of methylene chloride (20 ml), water (10 ml) and 36% aqueous formaldehyde (1 ml), followed by adjusting to pH 8.0 with 20% aqueous sodium carbonate. After stirring for 3 hours at 30°-35° C., the reaction mixture was further adjusted to pH 2.0 with 10% hydrochloric acid and then extracted with methylene chloride. The extract was washed with an aqueous sodium chloride dried over magnesium sulfate and then evaporated. The residue (0.46 g) was chromatographed on silica gel using a mixed solvent of benzene and ethyl acetate (2:1 by volume) as an eluent to obtain benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer)(0.14 g).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with an aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue (0.46 g) was chromatographed on silica gel using a mixed solvent of benzene and ethyl acetate (2:1 by volume) as an eluent

Sources & evidence

ORD record
ord-b1188ecee01247e4b914d48f497f5f2a
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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